Jamaica

$100+ Cheap flights from Chicago (CHI) to Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Feb 28 — Mar 71
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Jamaica with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Jamaica

Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This CheapOair deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/128:41 pm
ORD
-
KIN
1 stop14h 19m
Spirit Airlines
Thu 3/1912:17 pm
KIN
-
ORD
1 stop7h 29m
Spirit Airlines
Deal found 1/26$358
This FlightHub deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Fri 2/271:00 pm
MBJ
-
ORD
1 stop7h 11m
Spirit Airlines
Deal found 1/28$365
This CheapOair deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:16 pm
ORD
-
KIN
1 stop14h 44m
Spirit Airlines
Sun 3/1512:17 pm
KIN
-
ORD
1 stop23h 04m
Spirit Airlines
Deal found 1/27$365
This CheapOair deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:19 am
ORD
-
MBJ
2 stops24h 43m
Spirit Airlines
Fri 3/61:00 pm
MBJ
-
ORD
2 stops31h 47m
Spirit Airlines
Deal found 1/28$367
This CheapOair deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/18:43 pm
ORD
-
MBJ
1 stop14h 19m
Multiple Airlines
Sun 2/87:05 pm
MBJ
-
ORD
1 stop26h 05m
Multiple Airlines
Deal found 1/27$368
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/204:42 pm
ORD
-
MBJ
2 stops18h 20m
Multiple Airlines
Fri 2/271:00 pm
MBJ
-
ORD
1 stop7h 11m
Multiple Airlines
Deal found 1/28$369
This CheapOair deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:41 pm
ORD
-
KIN
1 stop14h 19m
Spirit Airlines
Sun 3/2212:17 pm
KIN
-
ORD
1 stop23h 04m
Spirit Airlines
Deal found 1/28$369
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Sat 2/281:00 pm
MBJ
-
ORD
2 stops12h 40m
Spirit Airlines
Deal found 1/27$370
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:51 pm
ORD
-
MBJ
2 stops39h 33m
Multiple Airlines
Thu 3/51:00 pm
MBJ
-
ORD
1 stop11h 05m
Multiple Airlines
Deal found 1/27$371
This Orbitz deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/192:00 pm
ORD
-
MBJ
1 stop21h 20m
Multiple Airlines
Sat 4/2512:00 pm
MBJ
-
ORD
1 stop7h 48m
Multiple Airlines
Deal found 1/27$372
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:51 pm
ORD
-
MBJ
2 stops16h 11m
Multiple Airlines
Sat 2/2812:40 pm
MBJ
-
ORD
1 stop10h 59m
Multiple Airlines
Deal found 1/27$373
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/85:01 pm
MDW
-
MBJ
2 stops18h 01m
Multiple Airlines
Thu 2/123:08 pm
MBJ
-
MDW
1 stop8h 26m
Multiple Airlines
Deal found 1/28$373

Find flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(CheapOair)

One-way from

$100
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$529

Good round-trip deal

$480 or less

Good one-way deal

$248 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
From Chicago (CHI) to Jamaica
One-way flight from Chicago (CHI) to Jamaica
Highest demand for flights based on searches. 5% potential increase in price ($36 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in January 2026
Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.
Price to beat on a one-way flight from Chicago (CHI) to Jamaica.

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Chicago

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 3/12

8:41 pm-11:00 am

1 stop14h 19m

Kingston Norman Manley

Thu 3/19

12:17 pm-7:46 pm

1 stop7h 29m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 2/25

6:15 am-2:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

Thu 2/26

3:25 pm-9:41 am

2 stops19h 16m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/23

2:05 pm-12:32 pm

2 stops21h 27m

Montego Bay Sangster Intl

Fri 2/27

2:00 pm-9:41 am

2 stops20h 41m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 3/18

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Wed 3/25

1:48 pm-6:13 pm

Nonstop4h 25m

$382

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 3/11

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 3/14

1:48 pm-6:13 pm

Nonstop4h 25m

$387

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 3/11

6:36 pm-11:00 am

1 stop16h 24m

Kingston Norman Manley

Mon 3/16

12:17 pm-10:36 am

1 stop22h 19m

$388

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 3/11

6:36 pm-11:00 am

1 stop16h 24m

Kingston Norman Manley

Tue 3/17

12:17 pm-10:36 am

1 stop22h 19m

$388

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/1

6:40 am-2:10 pm

1 stop6h 30m

Montego Bay Sangster Intl

Thu 3/5

2:00 pm-11:35 pm

1 stop10h 35m

$392

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 3/11

6:36 pm-11:00 am

1 stop16h 24m

Kingston Norman Manley

Thu 3/19

12:17 pm-7:46 pm

1 stop7h 29m

$394

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 3/12

8:41 pm-11:00 am

1 stop14h 19m

Kingston Norman Manley

Wed 3/18

12:17 pm-7:46 pm

1 stop7h 29m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Jamaica

What is the cheapest month to book a flight from Chicago to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $96). Flying from Chicago to Jamaica in March is currently the most expensive (average of $405). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to JM?

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from Chicago to Jamaica?

    A quick flight from Chicago to Jamaica can take about 4h 04m. Spirit Airlines provides one of the quickest options available for as low as $382. There are 1724 mi between Chicago and Jamaica. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Jamaica one-way?

    One-way options have recently been found by users for as low as $98 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $157 and American Airlines from $164 one-way.

  • What are the most popular routes from Chicago to Jamaica?

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $410 for a flight from Chicago to Jamaica. The cheapest flight overall is $170 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $261.

  • Can I find deals for flights from Chicago to Jamaica that include hotel bookings?

    Yes. In addition to deals on Chicago to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jamaica.

  • Can I find deals for business class flights from Chicago to Jamaica?

    Yes. Cheapflights offers flight deals from Chicago to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $96). Flying from Chicago to Jamaica in March is currently the most expensive (average of $405). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Chicago to Jamaica

Discover the top 6 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$434FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$662FlexibilityNo cancel feeOn-time62%
DeltaCheapest$178Average$607FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$356Average$595FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$419Average$666FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$531Average$724FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.